Ethanol → HCID 86707528, compound

HRID 339031Notes

Reaction equation

HRID 339031 reaction equation
[F:1][C:2]([F:26])([F:25])[C@H:3]([N:12]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13]1)[C:4]1[CH:5]=[N:6][C:7]([NH:10][NH2:11])=[CH:8][CH:9]=1.[C:27]([O:30][CH2:31][CH2:32][O:33][C:34]1[CH:35]=[CH:36][CH:37]=[C:38]2[C:43]=1[N:42]=[C:41]([CH3:44])[CH:40]=[CH:39]2)(=[O:29])[CH3:28].C(O)C.C(O)(=O)C.C(O)(=O)C.I(C1C=CC=CC=1)=O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[C:27]([O:30][CH2:31][CH2:32][O:33][C:34]1[CH:35]=[CH:36][CH:37]=[C:38]2[C:43]=1[N:42]=[C:41]([C:44]1[N:6]3[CH:5]=[C:4]([C@@H:3]([N:12]4[CH2:16][CH2:15][C@H:14]([NH:17][C:18]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:24])[CH2:13]4)[C:2]([F:25])([F:1])[F:26])[CH:9]=[CH:8][C:7]3=[N:10][N:11]=1)[CH:40]=[CH:39]2)(=[O:29])[CH3:28]

Participants

7

Reactant 5

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 70983851HCID 70983851, compoundHCID 73357407Acetic acid;iodosylbenzeneHCID 86707414tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate

Product 1

HCID 86707528HCID 86707528, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (0.48 g, 1.2 mmol) and 2-(2-methylquinolin-8-yloxy)ethyl acetate (0.30 g, 1.2 mmol) in ethanol (5.8 mL, 1.2 mmol) was allowed to stir at ambient temperature for 12 hours. The solvent was removed under reduced pressure. The residue was dissolved in dichloromethane (5.8 mL) and iodosobenzene diacetate (0.41 g, 1.3 mmol) was added. The reaction mixture was stirred at ambient temperature for 1 hour. Ethyl acetate (20 mL) and saturated sodium bicarbonate (10 mL) were added. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography on a C18 column (0-100% acetonitrile/water) to give the title compound (0.47 g, 66%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane (5.8 mL)
  3. stirringThe reaction mixture was stirred at ambient temperature for 1 hour
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by reverse phase chromatography on a C18 column (0-100% acetonitrile/water)

Sources & evidence

ORD record
ord-c094c9f4a38944cfbe88c76637bd1a6c
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

Loading…